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$2,294,000

Nestled in the heart of the Hudson Valley, this exceptional custom-built compound offers a rare blend of elegance, privacy, and ease. Set on 3.15 acres of beautifully landscaped grounds, the property unfolds as a true retreat—featuring a main residence with a heated three-car attached garage, a legal guest house, a commercial-sized detached garage, a heated in-ground pool, pool pavilion, and multiple outdoor living spaces designed for both quiet enjoyment and memorable gatherings. The 4,900+ square foot main residence is rich in detail and thoughtful design. A gracious entry foyer welcomes you into formal living and dining rooms, while the expansive open-concept family room, with its inviting fireplace, creates a warm and natural gathering place. The gourmet kitchen, appointed with granite countertops and stainless-steel appliances, is both functional and refined. A charming breakfast nook overlooks a spacious deck and the beautifully landscaped pool complex, offering a serene backdrop for everyday living. The first-floor primary suite is a private sanctuary, with tray ceiling, custom closets, a spa-like bath with soaking tub and separate shower, and private access from the bedroom to the rear deck. A formal dining room with winscot, crown molding and hardwood floors, a well-placed laundry room, powder room, and secondary staircase leading to the heated three-car garage complete the main level. Upstairs, three generously sized bedrooms and three full baths are complemented by a comfortable sitting nook and a dedicated home office, perfectly suited for remote work or creative pursuits. The fully finished walk-out lower level expands the home’s versatility, offering a second full kitchen, fitness area, home theater with seating for nine, and a full bath, along with ample storage and dedicated mechanical spaces. The detached 36' x 32' heated garage offers exceptional flexibility, complete with a second-floor office and full bath, ideal for workspace, hobbies, or additional storage. Attached, the beautifully designed two-story guest house provides a fully self-sufficient living experience, featuring a private entrance, covered stone patio, full kitchen, living room with a striking stone fireplace, laundry, and two and a half baths. With its own garden and dedicated parking, this space presents an outstanding opportunity for extended living or supplemental income (Airbnb approval was never used, but can be renewed). Outdoors, the property truly shines. The backyard is a private oasis centered around a 38' x 30' heated in-ground pool, framed by custom stonework, walkways, and mature plantings. The pool house, both heated and air-conditioned, includes a changing room and a well-appointed bath. A striking covered cabana/gazebo features built-in seating and a full outdoor kitchen, complete with gas grill, refrigerator, microwave, and sink ... creating an effortless setting for summer entertaining. Additional features enhance both charm and functionality, including a small vegetable/herb garden, a gas fire pit, invisible fencing, and a custom-built kennel or chicken coop. A second gated driveway, discreetly positioned behind a stacked-stone retaining wall, provides convenient access for RV, boat, or guest parking. Extensive upgrades include 9-foot and vaulted ceilings, radiant floor heating on levels 1 and 2 (including the attached garage), Marvin Integrity windows, a high-efficiency Viessmann boiler, crown molding, LED recessed lighting, and spray foam insulation—ensuring comfort and energy efficiency year-round. Ideally located just minutes from the Taconic Parkway, Rhinebeck, and Red Hook, as well as area golf courses, wineries, spas, and fine dining, this one-of-a-kind property offers a seamless balance of seclusion and accessibility. Situated within the Red Hook Central School District.

4 Beds ⋅ 6 Baths ⋅ 988928 MLS

Nestled in the heart of the Hudson Valley, this exceptional custom-built compound offers a rare blend of elegance, privacy, and ease. Set on 3.15 acres of beautifully landscaped grounds, the property unfolds as a true retreat—featuring a main residence with a heated three-car attached garage, a legal guest house, a commercial-sized detached garage, a heated in-ground pool, pool pavilion, and multiple outdoor living spaces designed for both quiet enjoyment and memorable gatherings. The 4,900+ square foot main residence is rich in detail and thoughtful design. A gracious entry foyer welcomes you into formal living and dining rooms, while the expansive open-concept family room, with its inviting fireplace, creates a warm and natural gathering place. The gourmet kitchen, appointed with granite countertops and stainless-steel appliances, is both functional and refined. A charming breakfast nook overlooks a spacious deck and the beautifully landscaped pool complex, offering a serene backdrop for everyday living. The first-floor primary suite is a private sanctuary, with tray ceiling, custom closets, a spa-like bath with soaking tub and separate shower, and private access from the bedroom to the rear deck. A formal dining room with winscot, crown molding and hardwood floors, a well-placed laundry room, powder room, and secondary staircase leading to the heated three-car garage complete the main level. Upstairs, three generously sized bedrooms and three full baths are complemented by a comfortable sitting nook and a dedicated home office, perfectly suited for remote work or creative pursuits. The fully finished walk-out lower level expands the home’s versatility, offering a second full kitchen, fitness area, home theater with seating for nine, and a full bath, along with ample storage and dedicated mechanical spaces. The detached 36' x 32' heated garage offers exceptional flexibility, complete with a second-floor office and full bath, ideal for workspace, hobbies, or additional storage. Attached, the beautifully designed two-story guest house provides a fully self-sufficient living experience, featuring a private entrance, covered stone patio, full kitchen, living room with a striking stone fireplace, laundry, and two and a half baths. With its own garden and dedicated parking, this space presents an outstanding opportunity for extended living or supplemental income (Airbnb approval was never used, but can be renewed). Outdoors, the property truly shines. The backyard is a private oasis centered around a 38' x 30' heated in-ground pool, framed by custom stonework, walkways, and mature plantings. The pool house, both heated and air-conditioned, includes a changing room and a well-appointed bath. A striking covered cabana/gazebo features built-in seating and a full outdoor kitchen, complete with gas grill, refrigerator, microwave, and sink ... creating an effortless setting for summer entertaining. Additional features enhance both charm and functionality, including a small vegetable/herb garden, a gas fire pit, invisible fencing, and a custom-built kennel or chicken coop. A second gated driveway, discreetly positioned behind a stacked-stone retaining wall, provides convenient access for RV, boat, or guest parking. Extensive upgrades include 9-foot and vaulted ceilings, radiant floor heating on levels 1 and 2 (including the attached garage), Marvin Integrity windows, a high-efficiency Viessmann boiler, crown molding, LED recessed lighting, and spray foam insulation—ensuring comfort and energy efficiency year-round. Ideally located just minutes from the Taconic Parkway, Rhinebeck, and Red Hook, as well as area golf courses, wineries, spas, and fine dining, this one-of-a-kind property offers a seamless balance of seclusion and accessibility. Situated within the Red Hook Central School District.

163 Hapeman Hill Road, Red Hook

$669,900

Large, protective, ancient trees and handcrafted, artisan-made, stone walls beckon you towards this well-built, nearly 200-year-old, classic Red Hook farmhouse. This 4 Bedroom home has 3 full baths and a large bonus sunroom overlooking the yard, perfect as a private guest suite or home office with a designated entrance and full bath. The expansive 10.1-acre parcel boasts a cherry and peach tree, a spring-fed pond, a meandering stream, and acres of private woods to explore and make trails in. There is enough space for horses. Wood beams and historic remnants mark an old barn site near the pond. The unusually large, fully-fenced-in yard has iron fencing and a patio for entertaining, with ample space for a garden and a pool if desired. There are 3 bedrooms upstairs with a bathroom with pocket doors leading to the main bedroom. Laundry is upstairs as well. There is a bedroom on the first floor that could also be used as a den or library with the original hardwood flooring. The main floor has an open kitchen leading to the dining area and opening to the living room. Some of the many upgrades include new renovated bathrooms, a new roof with a warranty as of 2026, reinforced basement and stonework, updated hot-water heater, central-air, a full-house water filtration system, a storage shed that matches the home, and a Janelli security system. This is a genuinely solid home, built to last, on pastoral grounds filled with history and acres to explore. The location is perfectly serene and an ideal refuge, yet 10-minutes to the center of town. Williams Road is arguably one of the most beautiful roads in Red Hook and is quiet enough for long walks, biking, and jogging. Close to Tivoli, Bard, Rhinebeck, and the Taconic.

4 Beds ⋅ 3 Baths ⋅ 986710 MLS

Large, protective, ancient trees and handcrafted, artisan-made, stone walls beckon you towards this well-built, nearly 200-year-old, classic Red Hook farmhouse. This 4 Bedroom home has 3 full baths and a large bonus sunroom overlooking the yard, perfect as a private guest suite or home office with a designated entrance and full bath. The expansive 10.1-acre parcel boasts a cherry and peach tree, a spring-fed pond, a meandering stream, and acres of private woods to explore and make trails in. There is enough space for horses. Wood beams and historic remnants mark an old barn site near the pond. The unusually large, fully-fenced-in yard has iron fencing and a patio for entertaining, with ample space for a garden and a pool if desired. There are 3 bedrooms upstairs with a bathroom with pocket doors leading to the main bedroom. Laundry is upstairs as well. There is a bedroom on the first floor that could also be used as a den or library with the original hardwood flooring. The main floor has an open kitchen leading to the dining area and opening to the living room. Some of the many upgrades include new renovated bathrooms, a new roof with a warranty as of 2026, reinforced basement and stonework, updated hot-water heater, central-air, a full-house water filtration system, a storage shed that matches the home, and a Janelli security system. This is a genuinely solid home, built to last, on pastoral grounds filled with history and acres to explore. The location is perfectly serene and an ideal refuge, yet 10-minutes to the center of town. Williams Road is arguably one of the most beautiful roads in Red Hook and is quiet enough for long walks, biking, and jogging. Close to Tivoli, Bard, Rhinebeck, and the Taconic.

176 Williams Road, Red Hook

$2,895,000

A study in proportion, light, and restraint, this under-construction residence, designed by Incorporated Architecture and Design and developed by ROAM Properties, is set back across seven acres within a private community in Red Hook, New York, where meadow and woodland converge at the edge of the Hudson Valley. Two wood-clad volumes anchor the composition, their silhouettes inspired by vernacular forms yet rendered with precision and clarity. The architecture is quiet but deliberate, designed to recede into the landscape while opening fully to it. At the center of the home, a dramatic 30-foot vaulted living and dining room rises in a single uninterrupted gesture. Natural light moves across pale plaster walls and wide-plank European oak floors, shifting the atmosphere throughout the day. A wood-burning stove grounds the space, bringing warmth and intimacy to the soaring volume. The kitchen is integrated rather than announced, wrapped in custom oak cabinetry and stone, with Thermador appliances discreetly concealed within. Just beyond, a wet bar allows the home to move effortlessly from daily living to evening entertaining. The residence offers four bedrooms and four-and-a-half baths, arranged with a strong sense of rhythm, privacy, and ease. A first-floor primary suite is complemented by a separate guest suite with its own kitchenette, creating comfort and autonomy for visitors. A den, reading nook, and office introduce quieter moments throughout the home and provide ample flexibility for working remotely. Bathrooms are finished in porcelain and stone surfaces with radiant heat underfoot. The primary suite is intentionally pared back, featuring a walk-in rain shower and a freestanding tub positioned to capture filtered light from the surrounding forest. Outside, terraces extend from the main living spaces into the meadow, where a 20-by-40 heated saltwater pool sits just beyond. The transition between architecture and landscape feels seamless, less a boundary than a gradient. Built with a high-performance envelope and thoughtfully selected materials throughout, the home balances architectural clarity with long-term livability. Quietly confident and deeply considered, 60 Stone Wall Path offers a rare opportunity just minutes from the villages of Red Hook and Rhinebeck, approximately 90 minutes from New York City, and moments from the Taconic State Parkway, an ideally situated home base from which to explore the very best of the Hudson Valley. Expected completion: December 2026.

4 Beds ⋅ 5 Baths ⋅ 982890 MLS

A study in proportion, light, and restraint, this under-construction residence, designed by Incorporated Architecture and Design and developed by ROAM Properties, is set back across seven acres within a private community in Red Hook, New York, where meadow and woodland converge at the edge of the Hudson Valley. Two wood-clad volumes anchor the composition, their silhouettes inspired by vernacular forms yet rendered with precision and clarity. The architecture is quiet but deliberate, designed to recede into the landscape while opening fully to it. At the center of the home, a dramatic 30-foot vaulted living and dining room rises in a single uninterrupted gesture. Natural light moves across pale plaster walls and wide-plank European oak floors, shifting the atmosphere throughout the day. A wood-burning stove grounds the space, bringing warmth and intimacy to the soaring volume. The kitchen is integrated rather than announced, wrapped in custom oak cabinetry and stone, with Thermador appliances discreetly concealed within. Just beyond, a wet bar allows the home to move effortlessly from daily living to evening entertaining. The residence offers four bedrooms and four-and-a-half baths, arranged with a strong sense of rhythm, privacy, and ease. A first-floor primary suite is complemented by a separate guest suite with its own kitchenette, creating comfort and autonomy for visitors. A den, reading nook, and office introduce quieter moments throughout the home and provide ample flexibility for working remotely. Bathrooms are finished in porcelain and stone surfaces with radiant heat underfoot. The primary suite is intentionally pared back, featuring a walk-in rain shower and a freestanding tub positioned to capture filtered light from the surrounding forest. Outside, terraces extend from the main living spaces into the meadow, where a 20-by-40 heated saltwater pool sits just beyond. The transition between architecture and landscape feels seamless, less a boundary than a gradient. Built with a high-performance envelope and thoughtfully selected materials throughout, the home balances architectural clarity with long-term livability. Quietly confident and deeply considered, 60 Stone Wall Path offers a rare opportunity just minutes from the villages of Red Hook and Rhinebeck, approximately 90 minutes from New York City, and moments from the Taconic State Parkway, an ideally situated home base from which to explore the very best of the Hudson Valley. Expected completion: December 2026.

60 Stone Wall Path, Red Hook

$6,995,000

Crestline is a visionary to-be-built residence offering 6,216 finished square feet of meticulously designed living space, including three bedroom suites and four-and-a-half luxurious baths. Pricing has been thoughtfully recalibrated to reflect the finalized construction scope and delivery approach, presenting an exceptional opportunity to secure a landmark Hudson Valley residence with enduring architectural and lifestyle value. Perched atop a private 41-acre hilltop with commanding 360-degree views of the Catskills, Stissing Mountain, and the rolling agricultural valleys below, Crestline is an architectural statement that harmonizes seamlessly with its natural surroundings. Located just minutes from Rhinebeck and Red Hook—celebrated for boutique shopping and farm-to-table dining—the property also offers effortless access to the Taconic State Parkway, placing New York City approximately 90 minutes away. Surrounded by protected farmland and open countryside, Crestline enjoys rare privacy while remaining close to hiking trails, antique markets, and the recreational offerings of the Hudson River Valley. The home’s architecture unfolds in two distinct volumes connected by a soaring triple-height glass foyer that creates a dramatic sense of arrival. The west-facing pavilion, a glass-wrapped structure that appears to float above the land, contains open-plan living and entertaining spaces designed to showcase sweeping Catskill views. Inside, 13-foot ceilings and expansive floor-to-ceiling windows flood the living room, gourmet kitchen, dining area, and library with natural light. A refined fluted-glass and steel partition subtly separates the kitchen from the dining area, while a dual-sided fireplace provides warmth between dining and great room. The library overlooks the pool and landscape, offering a tranquil retreat. Below this pavilion, inset into the slope, is a lower-level lounge and a separate pool house with full bath and sauna. The eastern volume, grounded in stone and wood, houses the private living quarters. The main level features a screening room and a serene primary suite with spa-like bath, dual walk-in closets, fireplace, and access to a secluded terrace. Upstairs, a family room and two spacious bedrooms, each with ensuite baths and walk-in closets, create a quiet retreat. Outdoor living is fully integrated into the design. A hardscaped kitchen and dining terrace with retractable shade structures extends from the foyer and great room, ideal for alfresco entertaining. The west-facing pool deck steps gracefully down the slope, aligning with the lower lounge and pool house, and includes shaded seating with a fireplace and sun-drenched lounging areas. Two rooftop gardens provide additional outdoor escapes with sweeping views. Hand-laid stone feature walls define the architectural experience, weaving indoors and out to anchor fireplaces, outdoor cooking areas, and a wet bar, while forming a stone-lined entry vestibule. A floating steel, wood, and glass staircase rises through the foyer beneath a skylight. Interior finishes reflect a modern yet grounded sensibility, pairing wide-plank oak floors and rift-cut walnut cabinetry with quartzite countertops, marble baths, and burnished brass accents. The exterior combines glass curtain wall, anodized bronze, and sustainable Accoya wood. Crestline is fully electric and sustainably designed, featuring geothermal heating and cooling, triple-pane windows, high-grade insulation, and energy-efficient systems throughout. From quiet evenings in the library to weekend gatherings around the pool, Crestline offers a rare balance of architectural distinction, immersive views, and privacy. This is not simply a home—it is a retreat where architecture and nature exist in perfect harmony.

3 Beds ⋅ 5 Baths ⋅ 948111 MLS

Crestline is a visionary to-be-built residence offering 6,216 finished square feet of meticulously designed living space, including three bedroom suites and four-and-a-half luxurious baths. Pricing has been thoughtfully recalibrated to reflect the finalized construction scope and delivery approach, presenting an exceptional opportunity to secure a landmark Hudson Valley residence with enduring architectural and lifestyle value. Perched atop a private 41-acre hilltop with commanding 360-degree views of the Catskills, Stissing Mountain, and the rolling agricultural valleys below, Crestline is an architectural statement that harmonizes seamlessly with its natural surroundings. Located just minutes from Rhinebeck and Red Hook—celebrated for boutique shopping and farm-to-table dining—the property also offers effortless access to the Taconic State Parkway, placing New York City approximately 90 minutes away. Surrounded by protected farmland and open countryside, Crestline enjoys rare privacy while remaining close to hiking trails, antique markets, and the recreational offerings of the Hudson River Valley. The home’s architecture unfolds in two distinct volumes connected by a soaring triple-height glass foyer that creates a dramatic sense of arrival. The west-facing pavilion, a glass-wrapped structure that appears to float above the land, contains open-plan living and entertaining spaces designed to showcase sweeping Catskill views. Inside, 13-foot ceilings and expansive floor-to-ceiling windows flood the living room, gourmet kitchen, dining area, and library with natural light. A refined fluted-glass and steel partition subtly separates the kitchen from the dining area, while a dual-sided fireplace provides warmth between dining and great room. The library overlooks the pool and landscape, offering a tranquil retreat. Below this pavilion, inset into the slope, is a lower-level lounge and a separate pool house with full bath and sauna. The eastern volume, grounded in stone and wood, houses the private living quarters. The main level features a screening room and a serene primary suite with spa-like bath, dual walk-in closets, fireplace, and access to a secluded terrace. Upstairs, a family room and two spacious bedrooms, each with ensuite baths and walk-in closets, create a quiet retreat. Outdoor living is fully integrated into the design. A hardscaped kitchen and dining terrace with retractable shade structures extends from the foyer and great room, ideal for alfresco entertaining. The west-facing pool deck steps gracefully down the slope, aligning with the lower lounge and pool house, and includes shaded seating with a fireplace and sun-drenched lounging areas. Two rooftop gardens provide additional outdoor escapes with sweeping views. Hand-laid stone feature walls define the architectural experience, weaving indoors and out to anchor fireplaces, outdoor cooking areas, and a wet bar, while forming a stone-lined entry vestibule. A floating steel, wood, and glass staircase rises through the foyer beneath a skylight. Interior finishes reflect a modern yet grounded sensibility, pairing wide-plank oak floors and rift-cut walnut cabinetry with quartzite countertops, marble baths, and burnished brass accents. The exterior combines glass curtain wall, anodized bronze, and sustainable Accoya wood. Crestline is fully electric and sustainably designed, featuring geothermal heating and cooling, triple-pane windows, high-grade insulation, and energy-efficient systems throughout. From quiet evenings in the library to weekend gatherings around the pool, Crestline offers a rare balance of architectural distinction, immersive views, and privacy. This is not simply a home—it is a retreat where architecture and nature exist in perfect harmony.

151 Rowe Road, Red Hook

$3,999,000

Nearly 30 secluded acres of rolling meadows and woodlands unfold into breathtaking panoramic views of the Catskill Mountains. This is a place to slow down and reconnect. Reminiscent of the Adirondack Great Lodges, this home is a masterful blend of rustic elegance and timeless craftsmanship. Soaring, strap-and-beam ceilings create a dramatic sense of space, while a custom-crafted staircase and a floor-to-ceiling wood-burning stone fireplace add to the home's warmth and grandeur. Step from the main living area out onto the brick patio to take in sweeping sunset views over the mountains. The expansive dining room easily accommodates large gatherings, and features a cozy window seat ideal for lounging while soaking in the views. The chef’s kitchen is both stylish and functional, featuring a beamed tin ceiling, tile flooring, and stone countertops that lend a timeless elegance. Just off the kitchen, step into your private outdoor oasis. This expansive patio features a pergola draped in mature, blooming wisteria. At the heart of the space is a fully equipped built-in barbecue station perfect for hosting al fresco dinners or weekend cookouts. A half bath, laundry room, and walk-in pantry offer added convenience, leading directly to the attached garage. The first-floor primary ensuite has westerly mountain vistas, direct access to its own private deck, and a secluded outdoor shower. Three additional bedrooms and a full bath provide ample space for family and guests. The second floor offers additional privacy and flexibility, featuring a second primary ensuite complete with a private balcony. Two more bedrooms with balconies, a full bath, and a cozy reading nook create a warm and welcoming retreat. The heated gunite pool and pool house, complete with a full bath and kitchen, are perfectly positioned to capture all-day sunlight while maintaining complete privacy. Tucked away for privacy, the Vermont Post and Beam barn adds both character and versatility to the property. Outfitted with electric and a full second-story loft, it features eaved windows that flood the space with natural light. This exceptional property exudes quiet rustic elegance, with spacious living areas, rolling lawns, and dramatic Catskill Mountain views. Located in the northeast area of Dutchess County with easy access to Red Hook, Rhinebeck, Pine Plains, Millbrook, Tivoli, Germantown, Hudson and more. Convenient to trains, Fisher Center, Bard College, private airports, excellent restaurants, farmers markets and more.

6 Beds ⋅ 6 Baths ⋅ 921530 MLS

Nearly 30 secluded acres of rolling meadows and woodlands unfold into breathtaking panoramic views of the Catskill Mountains. This is a place to slow down and reconnect. Reminiscent of the Adirondack Great Lodges, this home is a masterful blend of rustic elegance and timeless craftsmanship. Soaring, strap-and-beam ceilings create a dramatic sense of space, while a custom-crafted staircase and a floor-to-ceiling wood-burning stone fireplace add to the home's warmth and grandeur. Step from the main living area out onto the brick patio to take in sweeping sunset views over the mountains. The expansive dining room easily accommodates large gatherings, and features a cozy window seat ideal for lounging while soaking in the views. The chef’s kitchen is both stylish and functional, featuring a beamed tin ceiling, tile flooring, and stone countertops that lend a timeless elegance. Just off the kitchen, step into your private outdoor oasis. This expansive patio features a pergola draped in mature, blooming wisteria. At the heart of the space is a fully equipped built-in barbecue station perfect for hosting al fresco dinners or weekend cookouts. A half bath, laundry room, and walk-in pantry offer added convenience, leading directly to the attached garage. The first-floor primary ensuite has westerly mountain vistas, direct access to its own private deck, and a secluded outdoor shower. Three additional bedrooms and a full bath provide ample space for family and guests. The second floor offers additional privacy and flexibility, featuring a second primary ensuite complete with a private balcony. Two more bedrooms with balconies, a full bath, and a cozy reading nook create a warm and welcoming retreat. The heated gunite pool and pool house, complete with a full bath and kitchen, are perfectly positioned to capture all-day sunlight while maintaining complete privacy. Tucked away for privacy, the Vermont Post and Beam barn adds both character and versatility to the property. Outfitted with electric and a full second-story loft, it features eaved windows that flood the space with natural light. This exceptional property exudes quiet rustic elegance, with spacious living areas, rolling lawns, and dramatic Catskill Mountain views. Located in the northeast area of Dutchess County with easy access to Red Hook, Rhinebeck, Pine Plains, Millbrook, Tivoli, Germantown, Hudson and more. Convenient to trains, Fisher Center, Bard College, private airports, excellent restaurants, farmers markets and more.

926 Turkey Hill Road, Red Hook